Hexane → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-fluorophenyl)oxindole
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].[Li]CCCC.CCCCCC.[CH2:20]([N:22]([CH2:41][CH3:42])[CH2:23][CH2:24][N:25]1[C:35]2[C:30](=[C:31]([C:37]([F:40])([F:39])[F:38])[CH:32]=[C:33]([I:36])[CH:34]=2)[C:28](=[O:29])[C:26]1=[O:27])[CH3:21]>C1COCC1>[CH2:41]([N:22]([CH2:20][CH3:21])[CH2:23][CH2:24][N:25]1[C:35]2[C:30](=[C:31]([C:37]([F:38])([F:40])[F:39])[CH:32]=[C:33]([I:36])[CH:34]=2)[C:28]([OH:29])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[F:8])[C:26]1=[O:27])[CH3:42]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-bromo-2-fluorobenzene (0.09 mL, 0.823 mmol) in THF (4 mL) was added dropwise 1.53 N BuLi in hexane (0.54 mL, 0.826 mmol) over 10 min at −78° C. and the mixture was stirred for 10 min. The resulting solution was then transferred into the cooled solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodoisatin (330 mg, 0.75 mmol) in THF (2 mL) at −78° C. via a cannula. The mixture was stirred for 30 min at the same temperature and the reaction was quenched with aqueous NaHCO3. The mixture was extracted with ethyl acetate and the extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 50:1 to 30:1 chloroform/methanol to give the title compound (35.9 mg, 9%).
Workup
- stirringThe mixture was stirred for 30 min at the same temperature
- customthe reaction was quenched with aqueous NaHCO3
- extractionThe mixture was extracted with ethyl acetate
- dry with materialthe extracts were dried over MgSO4
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography with 50:1 to 30:1 chloroform/methanol
Sources & evidence
- ORD record
- ord-26078de1480b478daf05cabc3caf957a
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06576656B1
Reaction notes
Loading…